A wishbone never breaks evenly, and neither does a heart—at least, that’s what Conan Gray muses on his fourth album, Wishbone, which dropped on August 15. The project was two years in the making and came to the singer-songwriter unexpectedly while touring his ’80s-inspired pop extravaganza, Found Heaven, as he was healing through the pitfalls of heartbreak.
In May, he kick-started the Wishbone era with the swoonworthy romance of “This Song,” which is a confession of love fueled by yearning. The album begins as a grand gesture filled with highs and eventually tumbles down into the lows of his relationships, be it with romantic prospects, his self-image, or family dynamics. In “Class Clown,” he admits to feeling an “unexplainable” looming emotion that followed him from his upbringing in Texas to global superstardom. “Nauseous” expands upon that, exploring how childhood trauma has affected his adult relationships.
“Being this honest in all of the music feels new again,” Conan says, sitting down after posing for photos in Cosmo’s studio. “It was a very raw and humbling experience because I forgot how strange it feels to truly sing about your deepest, darkest, intimate moments of life.”
For the 26-year-old, Wishbone is a homecoming in more ways than one. His music video trilogy for “This Song,” “Vodka Cranberry,” and “Caramel” recreates a dream-scape version of his coming-of-age story mixed with his fantasies of real-life romance. It visually calls back to his debut single, “Idle Town,” a melodically moody track inspired by his upbringing in Georgetown, Texas, and embraces the rawness of his roots on songs like “Heather” and “People Watching.”
Letting loose in his music has clearly worked in his favor, as he drew in one of the largest crowds New York’s Governors Ball has ever seen in 2025. He has the sort of relatability that rakes in more than 54 million monthly listeners on Spotify and earns him the number one spot of top global albums on the platform.
As he sits before me at the Cosmopolitan office in a worn-in Stanford t-shirt and light-washed jeans, it feels more like a catch-up with an old friend as he asks how I drink my coffee. We discussed how he heals through heartbreak and how he hopes listeners muscle through their own in streaming his latest album. He’s also seen a bunch of fan fiction inspired by him and his music—and he wants more.
When you first announced Wishbone, you said you didn’t want people to hear it. What made you feel like you had to keep it hidden?
It wasn’t necessarily that I didn’t want people to hear it but more like I didn’t expect them to. I was in the middle of releasing my third album when I started working on Wishbone, and I truly was writing for myself. I had some things that I wanted to say that had been stressing me the fuck out and I just had to get them off my chest. That’s mainly the reason why—because I wasn’t planning on it.
It was more of a release for you.
Fully. People always ask me, “Do you keep a diary? It’s so good for your brain.” I basically do because I write songs. That’s my way of journaling.
How are you feeling about it now that everything’s out and being listened to?
It’s still pretty surreal that it’s even out. There was a beauty in my third album because it was distinctly different from anything I had ever done, and I felt a certain ability to not be judged. During that whole era, I got to play a character and hide behind this very experimental time of my life.
Being this honest in all of the music feels new again. It was a very raw and humbling experience because I forgot how strange it feels to truly sing about your deepest, darkest, intimate moments of life. When I was in rehearsals for my tour, they played me the arrangement they made for “Class Clown.” The second we started getting into it and I tried to sing the first words, I fully started crying. I forgot that’s how it feels and that I was actually going to say everything that I was saying on the album.
It feels like the beginning for your listeners, but you’ve lived with this album for almost two years. What’s the first thing you do after finishing a project? Do you have any traditions?
I am very severe about finishing a piece of work. I don’t let myself have any fun until I’ve gotten absolutely everything done. There’s still a lot left to do with the tour coming up. I just feel extremely grateful that everything’s been received with so much love and understanding and that people relate. That’s a huge relief, because I really put myself out there and I’m always a little afraid that maybe it’s just me that feels those emotions I write about.
You’re definitely not the only one going through those feelings. As a listener, I was like, “Oh, I’ve never had an original experience in my life.”
No, never. Ugh, we’re so unoriginal. The fact that we all think we’re different from each other is what makes us all the same. You know? Because we all think we’re the only ones.
The fact that we all think we’re different from each other is what makes us all the same.
—Conan Gray
Did you share any of your songs with friends or people who weren’t directly involved in the project?
I have a good chunk of friends who don’t make music and don’t care about my career other than they hope that I’m doing well. Those are the people I get my most important opinions from. Ashley—who has been my best friend since we were 11—I play her everything, and she tells me very honestly what she thinks. It’s important to have a diverse friend group, too, because there’s a huge difference between musicians’ music and music for the people. My goal is to connect with people because I was such a lonely kid. Everyone has a different reason to create, and mine was always companionship.
You’ve also given and received support from other musicians, like Role Model and Charli XCX. What are those relationships like? Do they just hit you up, like, “Want to do the ‘Apple’ dance?”
I had been to Tucker [aka Role Model]’s show in L.A., and I knew about the Sally of it all. I had asked, and then we planned to be as fun and ridiculous as possible. For “Apple,” I also just reached out to Charli, like, “Hey, please, please, please, can I be the Apple girl?” and she agreed because she’s the nicest girl ever. She’s been so kind to me from the beginning of my career, always had words of encouragement, and believed in me. It meant a lot, especially when I just started. She is such a legend and has been doing her thing for so long, and I really thank her.
Let’s talk about the Wishbone cinematic universe you’ve built through “This Song,” “Vodka Cranberry,” and “Caramel.” Was carving out this visual narrative always part of the project, or was it something that came to you after you wrote each track?
I wanted to tell a classic love story. The music videos are a manifestation of something that I wish I could have had in high school. I wasn’t falling in love, wrestling in creeks, and kissing on rooftops. I was studying for AP tests and writing songs in my bedroom. In a way, it was making a dream come true for me. I wanted to give people a piece of that dream and let them see a world in which two people fall in love and it works out.
It really emphasizes that young summer love, coming-of-age vibe. It almost reminds me of movies like The Last Song or The Incredibly True Adventure of Two Girls in Love, and—I can’t believe I’m saying this—it could be the new-gen version of Troye Sivan’s Blue Neighbourhood trilogy.
Look, put respect on the scripture!
Did you have any specific influences when bringing the visuals to life?
For sure—like a gajillion. It was all coming-of-age and romance movies. I’m not kidding, The Hannah Montana Movie was one of them.
So what I’m hearing is you’re having a Miley Stewart summer.
Like, Miley Stewart with her 13-inch extensions, riding her horse. It will forever be real. But I was also influenced by Normal People, which affected me deeply. Brokeback Mountain was another one, and my director, Danica Kleinknecht, had a bunch of other references I had never seen.
Why build this world and create these characters, Wilson and Brando? Do they represent anything in your personal story?
There are bits and pieces that are completely real moments from my own life, but also not even close to what happened. I wanted it to feel innately like a return to my hometown. I needed the videos to be shot in Texas so I could be as honest as possible. You can’t put me in Texas and then dress me in designer clothes. I was wearing clothes that I had in my closet from when I was 16. People have definitely picked up on that because my whole childhood is documented on the internet.
Your fans have started expanding the Wishbone universe online, with Wilson and Brando fan fiction on Wattpad. Have you read any of it? Is there any fan-made content that has stood out to you over the years?
I wasn’t a fan fiction ingester growing up, but there was one from when I was in high school where it was me and Tom Holland. But it wasn’t actually me; it was just my face on a character. It was several chapters about this relationship, and it was riveting. Me and my friends all read it together, and every time a new chapter would come out, we’d be like, “Oh my god, there’s a new one.” This was pre-Zendaya.
We need to call up the writer of that story right now.
I miss it. Bring it back! Update the Wattpad!
Back to your own characters—is this the end of Wilson and Brando’s journey, or will we see more of them eventually?
I would love to see more of them, but I don’t really know. At the moment, I’m focused on the tour.
Is there anything about the Wishbone pajama show that fans may be surprised by?
It’s my first tour with a storyline. I want to bring people through a lot of the feelings that I felt while I was making Wishbone, and that’s what the tour is going to feel like.
Can you give a little teaser of the setlist?
Look, “Maniac” is a banger. I’m going to sing it. “Vodka Cranberry” will be sung. “People Watching” will be sung—I actually will never forget singing it at Radio City. I’m going to hit all the hits, and then I’m gonna sing the new songs.
Speaking of your Radio City show, that was the first concert I went to solo, and I immediately felt a sense of community. The people next to me came all the way from Italy, and it was their first concert ever. What do you make of moments like these?
My shows are filled with a bunch of people who are exactly like me. When I hear stories of people coming to the shows and going out of their way to come see me, I’m like, “Hell yeah!” because we’re the same. It makes me feel less alone in the world, and it’s also hard for me to understand. My most important job is to write music that feels true to me and that will connect with people. If I think too hard about the fact that there are so many people watching, then I’m just going to say nothing.
I wanted to break people’s hearts and force them to go through the breakup with me.
—Conan Gray
Heartbreak and reflection are a throughline of your discography and this record, but you kicked off this era with a stunning, cinematic confession of love on “This Song.” Why go with that as the lead single for Wishbone?
It was a little bit of a psych-out. I selfishly wanted people to feel the same heartbreak that I did, and I started with “This Song” because it comes from a place of love and relationships start from a place of love. It’s butterflies; it’s happiness. It’s that summer love. It’s that happy “Oh my god, anything could happen. I’m so in love. Life’s so good” feeling. Then I wanted to break people’s hearts and force them to go through the breakup with me. When you listen to Wishbone from the top down, you really get a chronological order of what goes down.
You definitely go through the whole spectrum. There’s a specific line from “Connell” that evokes an opposite feeling from “This Song”: “And you remind me of how good it feels to hurt / Yeah, you remind me of how little I deserve.” How did you get to that point? Were you hesitant to include it at all?
In so many ways, this album caught me at a time of my life that was the straw that broke the camel’s back. It was that one final experience, that one final moment, that one final person, where I really took a step back and looked at my life and thought to myself, This is something that’s consistently happening to me. There’s nothing coincidental about this. That’s why in “Connell,” I ask, “Who’s the victim in the end?” If I’m constantly choosing people who I know are going to hurt me, maybe it’s just a me problem. I have to put myself in places where I’m gonna be loved, even though that’s scary.
It stings a certain way because you’re not necessarily villainizing the person who hurt you, but yourself in such a vulnerable state.
Especially if you grew up in a situation where rocky and confusing forms of love are what you’re used to. You inevitably look for something familiar in the next people that you go to. During the past two years, when I made Wishbone, I took a hard look at my life and was like, “Okay, never again. I’m not going to do this to myself anymore. That was the final time.” That’s why I got to write about it. In a way, I wanted to hold myself responsible—to never put myself in a place where I could be hurt like that.
Falling in love is one of the great things about being a human. You should never really stop yourself from doing it.
—Conan Gray
It really takes a toll when it happens to you. I had gone through this crazy heartbreak two years ago, around the time you started working on this record. Maybe it was the same time.
Maybe it was the same person…
Can you imagine? I hope not, for your sake. Once it ended, I questioned if I’d be capable of being in a relationship again, but one of my best friends reminded me of that old saying: “It’s better to have loved and lost than to never have loved at all.” Having been through it, I fully agree with it now.
It hurts so much less if you’ve already experienced it one time because you know you’re gonna be fine on the other end. Falling in love is one of the great things about being a human. You should never really stop yourself from doing it.
Get tickets for Conan’s ‘Wishbone’ Pajama Show tour
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Parts of this interview have been edited and condensed for clarity.
Creative director: Samantha Adler. Senior entertainment director: Maxwell Losgar. Visual director: Scott M. Lacey. Associate visual editor: Sabrina Toto.
